EP2467021B1 - Dérivés de 3-[1-(3-haloalkyl)-triazolyl]-phényle-sulfure en tant qu'acarides et insecticides - Google Patents

Dérivés de 3-[1-(3-haloalkyl)-triazolyl]-phényle-sulfure en tant qu'acarides et insecticides Download PDF

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Publication number
EP2467021B1
EP2467021B1 EP10742097.8A EP10742097A EP2467021B1 EP 2467021 B1 EP2467021 B1 EP 2467021B1 EP 10742097 A EP10742097 A EP 10742097A EP 2467021 B1 EP2467021 B1 EP 2467021B1
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EP
European Patent Office
Prior art keywords
methyl
spp
phenyl
carboxamide
chloro
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German (de)
English (en)
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EP2467021A1 (fr
Inventor
Bernd Alig
Stefan Antons
Reiner Fischer
Norbert Lui
Adeline KÖHLER
Arnd Voerste
Ulrich Görgens
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Bayer Intellectual Property GmbH
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Bayer Intellectual Property GmbH
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/22—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having nitrogen atoms of amidino groups further bound to nitrogen atoms, e.g. hydrazidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel 3- [1- (3-haloalkyl) -triazolyl] -phenyl-sulfide derivatives, their use as acaricides and insecticides for controlling animal pests and processes for their preparation.
  • the compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
  • the compounds of formula (I) optionally comprise diastereomers or enantiomers.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediyl or alkenyl may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • halogen is fluorine, chlorine, bromine and iodine, particularly preferably fluorine, chlorine and bromine, and very particularly preferably fluorine and chlorine.
  • the compounds of general formula (I) can be used with those in the application WO 1999/055668 be prepared methods described. By way of derogation from these methods described, the compounds of the formula (I) can also be prepared by processes (A) or (A ').
  • a 1 , B 0 , B 1 , B 2 , B 3 , R 1 and R 2 have the meanings given above and A 1a is alkyl, preferably (C 1 -C 6 ) alkyl.
  • Anilines of formula (VII) are either commercially available or can be prepared by known methods.
  • the anilines (VII) are converted with sodium nitrite in the presence of hydrochloric acid into the corresponding diazonium salts and then reduced with stannous chloride to give hydrazines of the formula (VI).
  • the hydrazines (VI) are converted into the corresponding hydrazides (V).
  • Hydrazides (V) are treated with formamidine hydrochloride in the presence of a base such as. B. sodium bicarbonate, wherein the triazoles of the formula (IV-A) are formed.
  • the hydrazines (VI) can be converted to the corresponding amidrazones of formula (X) in the presence of amidines of formula (XI) or salts thereof, such as amidinium hydrochlorides or sulfates.
  • Amidrazones of formula (X) are reacted with an orthoformate such as methyl orthoformate or ethyl orthoformate to form the triazoles of formula (IV-A).
  • the triazoles of the formula (IV-A) can also be prepared via copper-catalyzed coupling reaction with the boronic acids of the formula (VIII) and triazoles of the formula (IX-A) (cf.
  • a 1 , B 0 and B 2 have the abovementioned meaning and B 1 and B 3 are hydrogen.
  • Migdolus Spp. Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp., Popillia japonica, Premnotrypes spp., Psylliodes spp.
  • Ptinus spp. Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Starchus spp., Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp. Zabrus spp ..
  • Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lynmaea spp., Oncomelania spp., Pomacea spp., Succinea spp.
  • helminths e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum , Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Ne
  • protozoa such as Eimeria
  • Eimeria protozoa
  • Eurygaster spp. Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Monalonion atratum, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus spp.
  • Idioscopus spp. Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli,
  • Hymenoptera e.g. Athalia spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Lepidoptera From the order of Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius , Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnephasia spp., Conopomorph
  • Copitarsia spp. Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp.
  • Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
  • Thysanoptera e.g. Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Anaphothrips obscurus e.g. Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura e.g. Lepisma saccharina.
  • the plant parasitic nematodes include e.g. Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • the compounds according to the invention may also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents ( Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient Impregnated synthetic materials, fertilizers and Feinstverkapselitch in polymeric materials.
  • solutions emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient Impregnated synthetic materials, fertilizers and Feinstverkapselitch in polymeric materials.
  • the present invention therefore further relates to formulations and application forms prepared therefrom as crop protection agents and / or pesticides such.
  • B. drench, drip and spray comprising at least one of the active compounds according to the invention.
  • the use forms contain other crop protection agents and / or pesticides and / or the effect of improving adjuvants such as penetration enhancers, eg.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more active compounds according to the invention, further agrochemical active substances.
  • auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, such as adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself being a biological agent Has effect.
  • Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties.
  • Typical auxiliaries are: extenders, solvents and carriers.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives are for example protective colloids, Binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
  • the in the literature Baur et al., 1997, Pesticide Science 51, 131-152 ) method can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or Isotridecylethoxylat (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or Dianmionium hydrogen phosphate.
  • alcohol alkoxylates such as coconut oil ethoxylate (10) or Isotridecylethoxylat (12)
  • fatty acid esters such as rapeseed oil or soybean oil
  • fatty amine alkoxylates such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or Dianmionium hydrogen phosphate.
  • the formulations generally contain between 0.01 and 98% by weight of active ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in admixture with one or more suitable fungicides, bactericides, acaricides, nematicides, insecticides, microbiologicals, fertilizers, attractants, phytotonics, sterilants, synergists, safeners, semiochemicals and / or plant growth regulators, for example, in order to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent development of resistance. Furthermore, such combinations can improve plant growth, tolerance to abiotic factors such. As high or low temperatures, against dryness or increased water or Bodensalzgehalt.
  • flowering and fruiting behavior can be improved, germination and rooting optimized to facilitate harvest and increase crop yields, influence ripeness, increase the quality and / or nutritional value of harvested produce, extend shelf life and / or improve the workability of the harvested products.
  • synergistic effects are obtained by combining the active compounds according to the invention and the mixing partners, ie the effectiveness of the particular mixture is greater than the effectiveness of the individual components.
  • the combinations can be used both in pre-mix, tank or finished mixes and in seed applications.
  • Particularly favorable mixing partners are e.g. the following:
  • drugs with unknown mechanism of action such as azadirachtin, amidoflumet, benzoximate, bifenazate, quinomethionate, cryolites, cyflumetofen, dicofol, fluensulfone (5-chloro-2 - [(3,4,4-trifluorobut-3-en-1-yl) sulfonyl] -1,3-thiazoles), flufenerim, pyridalyl and pyrifluquinazone; furthermore preparations based on Bacillus firmus (I-1582, BioNeem, Votivo) and the following known active compounds
  • a mixture with other known active ingredients, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving the plant properties is possible.
  • the active compounds according to the invention can furthermore be present in the form of insecticides in their commercial formulations and in the formulations prepared from these formulations in admixture with synergists.
  • Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active compounds according to the invention may furthermore, when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations, be present in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
  • the application is done in a custom forms adapted to the application.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
  • plants and their parts can be treated.
  • wild-type or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the terms "parts” or “parts of plants” or “plant parts” have been explained above.
  • Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or enhancements of the activity spectrum and / or enhancement of the action of the substances and compositions which can be used according to the invention, better plant growth, are increased tolerance high or low temperatures, increased tolerance to dryness or to bottoms, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher harvest value of the harvested products, higher shelf life and / or workability of the harvested products that go beyond the actual expected effects.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or soil salinity, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher harvest value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
  • transgenic plants are the important crops such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
  • Traits which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins which are formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes CryIA (a) , CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations) in the plants (hereinafter "Bt plants”).
  • Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes which confer the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • SAR systemic acquired resistance
  • PAT phosphinotricin
  • Bt plants are maize, cotton, soya and Potato varieties known under the trade names YIELD GARD® (eg corn, cotton, soy), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato) to be expelled.
  • YIELD GARD® eg corn, cotton, soy
  • KnockOut® eg corn
  • StarLink® eg corn
  • Bollgard® cotton
  • Nucotn® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, eg rapeseed
  • IMI® tolerance against imidazolinone
  • STS® tolerance to sulfonylureas eg corn
  • Clearfield® varieties eg corn
  • the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active substance mixtures according to the invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
  • Nematocerina and Brachycerina eg Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.
  • Atylotus spp. Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia Spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. , Melophagus spp ..
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • arthropods are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • the use of the active compounds according to the invention takes place in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boluses, the feed-through process, suppositories, by parenteral administration, for example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, dipping or bathing (dipping), spraying, pouring (pour-on and spot-on), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boluses, the feed-through process, suppositories
  • parenteral administration for
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • the compounds according to the invention show a high insecticidal activity against insects which destroy industrial materials.
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
  • the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
  • the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cushions and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cushions and moth gels, as granules or dusts, in litter or bait stations.
  • the tin double salt is added in several portions to initially charged 100 g of sodium hydroxide solution (45%) and 100 g of water, the pH is adjusted to 14 and the hydrazine separated by multiple extraction with MTBE / ethyl acetate extraction from the aqueous phase. The solvent is in the Vacuum distilled off to obtain the hydrazine. After recrystallization from MTBE, 45 g (93% of theory) of pure 2,4-dimethylhydrazine are obtained M + : 136 1 H-NMR (D6-DMSO): 6.85-6.97 (m, 3H), 3.7 (m, 3H), 2.25 (s, 3H), 2.1 (s, 3H)
  • Step 2 N '- (2,4-dimethylphenyl) -2,2-difluoroacetohydrazide
  • Step 3 3- (Difluoromethyl) -1- (2,4-dimethylphenyl) -1H-1,2,4-triazole
  • Step 4 5- [3- (Difluoromethyl) -1H-1,2,4-triazol-1-yl] -2,4-dimethylbenzenesulfonyl chloride
  • Step 5 1,1 '- [Disulfanediylbis (4,6-dimethylbenzene-3,1-diyl)] bis [3- (difluoromethyl) -1H-1,2,4-triazole]
  • Step 6 3- (Difluoromethyl) -1- ⁇ 2,4-dimethyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl ⁇ -1H-1,2,4-triazole (Compound I-A-2)
  • Step 7 3- (Difluoromethyl) -1- ⁇ 2,4-dimethyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl ⁇ -1H-1,2,4-triazole (Compound I-A-4)
  • the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
  • the lambda-maX values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • the MH + signals were determined with an Agilent MSD system with ESI and positive or negative ionization.
  • the NMR spectra were determined on a Bruker Avance 400 equipped with a flow-through head (60 ⁇ l volume).
  • the solvent used was d 6 -DMSO or CD 3 CN, tetramethylsilane (0.00 ppm) being used as reference.
  • the measurement temperature is 303K if d 6 -DMSO is used as solvent and 298K if CD 3 CN is used as solvent.
  • the samples were determined with a Bruker Avance II 600 or III 600.
  • Boophilus microplus test (BOOPMI injection)
  • active compound 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.
  • the drug solution is injected into the abdomen (Boophilus microplus) , the animals are transferred to trays and stored in an air-conditioned room. The effect control takes place on storage of fertile eggs.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 20 ⁇ g / animal: IA-1, IA-2, IA-3, IA-4, 1-A-5, 1-A-7, 1-A-8, 1-A-9, 1-A-10, IA-11, IA-12, IA-17, IA-27, IA-36, IA-39
  • Solvent 78.0 Parts by weight of acetone 1.5 Parts by weight of dimethylformamide emulsifier: 0.5 Parts by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) .
  • Solvent 78.0 Parts by weight of acetone 1.5 Parts by weight of dimethylformamide Emulsifier: 0.5 Parts by weight of alkylaryl polyglycol ether
  • active compound preparation 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Bean leaf discs Phaseolus vulgaris
  • etranychus urticae Bean leaf discs infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • Solvent 78.0 Parts by weight of acetone 1.5 Parts by weight of dimethylformamide emulsifier: 0.5 Parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. Vessels are filled with sand, drug solution, Meloidogyne incognita egg larvae suspension and lettuce seed. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots. After 14 days, the nematicidal activity is determined by means of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to that of the untreated control.
  • Solvent 78.0 Parts by weight acetone 1.5 Parts by weight of dimethylformamide emulsifier: 0.5 Parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Bean leaf discs Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.

Claims (14)

  1. Dérivés de sulfure de 3-[1-(3-haloalkyl)-triazolyl]-phényle de formule (I)
    Figure imgb0099
     dans laquelle
    A1 représente CHF2,
    A2 représente hydrogène,
    B0 représente hydrogène, amino, halogène, cyano, nitro, alkyle, halogénoalkyle, alkylthio, halogénoalkylthio, alcoxy ou halogénoalcoxy,
    B1, B2, B3 représentent indépendamment les uns des autres hydrogène, halogène, cyano, nitro, alkyle, halogénoalkyle, cyanoalkyle, hydroxyalkyle, alcoxycarbonylalkyle, alcoxyalkyle, alcényle, halogénalcényle cyanoalcényle, alcynyle, halogénalcynyle, cyanoalcynyle, alcoxy, halogénalcoxy, cyanoalcoxy, alcoxycarbonylalcoxy, alcoxyalcoxy, alkylthio, halogénoalkylthio, alcoxyalkylthio, alkylsulfinyle, halogénoalkylsulfinyle, alcoxyalkylsulfinyle, alkylsulfonyle, halogénoalkylsulfonyle, alcoxyalkylsulfonyle, acyle, halogénoalkylcarbonyle, carboxyle, alcoxycarbonyle ou NR3R4, R3 et R4 représentant indépendamment l'un de l'autre hydrogène, alkyle, halogénoalkyle, cyanoalkyle, hydroxyalkyle, alcoxyalkyle, alkylthioalkyle, alcényle, halogénoalcényle, cyanoalcényle, alcynyle, halogénoalcynyle, cyanoalcynyle, acyle, alcoxycarbonyle, ou R3 et R4 pouvant former ensemble avec l'atome N auquel ils sont reliés un cycle saturé ou insaturé de cinq à huit éléments éventuellement substitué et éventuellement interrompu par des hétéroatomes,
    n représente le nombre 0, 1 ou 2,
    R1 représente hydrogène ou alkyle,
    R2 représente hydrogène, halogène, cyano, nitro, alkyle, halogénoalkyle, cyanoalkyle, alcoxyalkyle, alcényle, halogénoalcényle, alcynyle, halogénoalcynyle, halogénoalcoxyalkyle ; cycloalkyle ou cycloalcényle éventuellement substitué, éventuellement interrompu par un ou plusieurs hétéroatomes,
    les dérivés de sulfure de 3-[1-(3-haloalkyl)-triazolyl]-phényle de formule (I) n'étant pas le 3-(difluorométhyl)-1-{2,4-diméthyl-5-[(2,2,2-trifluoroéthyl)-sulfanyl]-phényl}-1H-1,2,4-triazol, le 3-(difluorométhyl)-1-{2,4-diméthyl-5-[(2,2,2-trifluoréthyl)-sulfinyl]-phényl}-1H-1,2,4-triazol, le 1-{5-[(2,2-difluoréthyl)sulfanyl]-2,4-diméthylphényl}-3-(difluorométhyl)-1H-1,2,4-triazol et le 1-{5-[(2,2-difluoréthyl)sulfinyl]-2,4-diméthylphényl}-3-(difluorométhyl)-1H-1,2,4-triazol.
  2. Composés de formule (I) selon la revendication 1, dans lesquels
    A1 représente CHF2,
    A2 représente hydrogène,
    B0 représente hydrogène, amino, halogène, cyano, nitro, alkyle en (C1-C6), halogénoalkyle en (C1-C6), alkylthio en (C1-C6), halogénoalkylthio en (C1-C6), alcoxy en (C1-C6) ou halogénoalcoxy en (C1-C6),
    B1, B2, B3 représentent indépendamment les uns des autres hydrogène, halogène, cyano, nitro, alkyle en (C1-C6), halogénoalkyle en (C1-C6), cyanoalkyle en (C1-C6), hydroxyalkyle en (C1-C6), alcoxycarbonyle en (C2-C7)-alkyle en (C1-C6), alcoxy en (C1-C6)-alkyle en (C1-C6), alcényle en (C2-C6), halogénalcényle en (C2-C6), cyanoalcényle en (C2-C6), alcynyle en (C2-C6), halogénalcynyle en (C2-C6), cyanoalcynyle en (C2-C6), alcoxy en (C1-C6), halogénalcoxy en (C1-C6), cyanoalcoxy en (C1-C6), alcoxycarbonyle en (C2-C5)-alcoxy en (C1-C6), alcoxy en (C1-C3)-alcoxy en (C1-C6), alkylthio en (C1-C6), halogénoalkylthio en (C1-C6), alcoxy en (C1-C3)-alkylthio en (C1-C6), alkylsulfinyle en (C1-C6), halogénoalkylsulfinyle en (C1-C6), alcoxy en (C1-C3)-alkylsulfinyle en (C1-C6), alkylsulfonyle en (C1-C6), halogénoalkylsulfonyle en (C1-C6), alcoxy en (C1-C3)-alkylsulfonyle en (C1-C6), acyle en (C1-C7), halogénoalkylcarbonyle en (C2-C5), carboxyle, alcoxycarbonyle en (C2-C7) ou NR3R4, R3 et R4 représentant indépendamment l'un de l'autre hydrogène, alkyle en (C1-C6), halogénoalkyle en (C1-C6), cyanoalkyle en (C1-C6), hydroxyalkyle en (C1-C6), alcoxy en (C1-C6)-alkyle en (C1-C6), alkylthio en (C1-C6)-alkyle en (C1-C6), alcényle en (C2-C6), halogénoalcényle en (C2-C6), cyanoalcényle en (C2-C6), alcynyle en (C2-C6), halogénoalcynyle en (C2-C6), cyanoalcynyle en (C2-C6), acyle en (C1-C7), alcoxycarbonyle en (C2-C7), ou R3 et R4 pouvant former ensemble avec l'atome N auquel ils sont reliés un cycle saturé ou insaturé à cinq ou six éléments éventuellement substitué par alkyle en (C1-C4), alcoxy en (C1-C4), halogénoalkyle en (C1-C4) et éventuellement interrompu par des hétéroatomes,
    n représente le nombre 0, 1 ou 2,
    R1 représente hydrogène ou alkyle en (C1-C4),
    R2 représente hydrogène, halogène, cyano, nitro, alkyle en (C1-C6), halogénoalkyle en (C1-C6), cyanoalkyle en (C1-C6), alcényle en (C2-C6), halogénoalcényle en (C2-C6), alcynyle en (C2-C6), halogénoalcynyle en (C2-C6), alcoxy en (C1-C6)-alkyle en (C1-C6), halogénoalcoxy en (C1-C6)-alkyle en (C1-C6) , cycloalkyle en (C3-C8) ou cycloalcényle en (C3-C8) éventuellement substitué, éventuellement interrompu par un ou plusieurs hétéroatomes.
  3. Procédé de fabrication de composés de formule (I) selon l'une quelconque des revendications 1 à 2, caractérisé en ce que
    (A) des anilines de formule (VII)
    Figure imgb0100
     sont mises en réaction avec du nitrite de sodium pour former des sels de diazonium, puis réduites en hydrazines de formule générale (VI)
    Figure imgb0101
    (B) les hydrazines de formule (VI) sont transformées en présence d'esters de formule (VIII)
    Figure imgb0102
     dans laquelle A1a représente alkyle, en hydrazides de formule générale (V)
    Figure imgb0103
    (C) les hydrazides de formule (V) sont mis en réaction avec du chlorhydrate de formamidine en présence d'une base pour former des triazoles de formule (IV-A)
    Figure imgb0104
    (D) les triazoles de formule générale (IV-A) sont transformés par sulfochloration en chlorures de sulfonyle de formule générale (III-A)
    Figure imgb0105
    (E) les chlorures de sulfonyle de formule (III-A) sont transformés par réduction en disulfures de formule générale (II-A)
    Figure imgb0106
    (F) les disulfures de formule générale (II-A) sont mis en réaction avec des électrophiles de formule générale (IX)
    Figure imgb0107
     dans laquelle AG représente un groupe partant tel que chlore, brome, tosylate, mésylate ou triflate,
    pour former des sulfures de formule générale (I-Aa)
    Figure imgb0108
    (G) les composés de formule (I-Aa) sont mis en réaction avec des oxydants pour former des sulfoxydes de formule générale (I-Ab)
    Figure imgb0109
     et des sulfones de formule générale (I-Ac)
    Figure imgb0110
     dans lesquelles A1, B0, B1, B2, B3, R1, R2 ont les significations selon l'une quelconque des revendications 1 à 2.
  4. Procédé selon la revendication 3, caractérisé en ce que
    les composés de formule générale (IV-A),
    dans laquelle A1, B0, B1, B2 et B3 ont les significations selon l'une quelconque des revendications 1 à 2,
    sont préparés par
    mise en réaction d'acides boroniques de formule générale (VIII)
    Figure imgb0111
     par une réaction de couplage catalysée par du cuivre, avec des triazoles de formule générale (IX-A)
    Figure imgb0112
     pour former les composés de formule (IV-A).
  5. Procédé selon la revendication 3, caractérisé en ce que
    les composés de formule générale (IV-A)
    dans laquelle A1, B0, B1, B2 et B3 ont les significations selon l'une quelconque des revendications 1 à 2,
    sont préparés par
    mise en réaction d'hydrazines de formule générale (VI)
    Figure imgb0113
     en présence d'amidines de formule (XI) ou leurs sels
    Figure imgb0114
     pour former des amidrazones de formule (X)
    Figure imgb0115
     et celles-ci sont mises en réaction avec un orthoformate pour former des triazoles de formule (IV-A).
  6. Composition d'agents actifs contenant au moins un dérivé de sulfure de 3-[1-(3-haloalkyl)-triazolyl]-phényle de formule (I) selon l'une quelconque des revendications 1 à 2, et au moins un autre agent actif insecticide, acaricide ou nématicide choisi dans le groupe constitué par
    (1) les inhibiteurs d'acétylcholinestérase (AChE), tels que par exemple
    les carbamates, p. ex. l'alanycarb, l'aldicarb, le bendiocarb, le benfuracarb, le butocarboxime, le butoxycarboxime, le carbaryl, le carbofurane, le carbosulfane, l'éthiofencarb, le fénobucarb, le formétanate, le furathiocarb, l'isoprocarb, le méthiocarb, le méthomyl, le métolcarb, l'oxamyl, le pirimicarb, le propoxur, le thiodicarb, le thiofanox, le triazamate, le triméthacarb, le XMC et le xylylcarb ; ou
    les organophosphates, p. ex. l'acéphate, l'azaméthiphos, l'azinphos (-méthyl, -éthyl), le cadusafos, le chloréthoxyfos, le chlorfenvinphos, le chlorméphos, le chlorpyrifos (-méthyl), le coumaphos, le cyanophos, le déméton-S-méthyl, le diazinon, le dichlorvos/DDVP, le dicrotophos, le diméthoate, le diméthylvinphos, le disulfoton, l'EPN, l'éthion, l'éthoprophos, le famphur, le fénamiphos, le fénitrothion, le fenthion, le fosthiazate, l'hepténophos, l'isofenphos, l'O-(méthoxyaminothio-phosphoryl)salicylate d'isopropyle, l'isoxathion, le malathion, le mécarbam, le méthamidophos, le méthidathion, le mévinphos, le monocrotophos, le naled, l'ométhoate, l'oxydéméton-méthyl, le parathion (-méthyl), le phenthoate, le phorate, la phosalone, le phosmet, la phosphamidone, le phoxim, le pirimiphos (-méthyl), le profénofos, le propétamphos, le prothiofos, le pyraclofos, le pyridaphenthion, le quinalphos, le sulfotep, le tébupirimfos, le téméphos, le terbufos, le tétrachlorvinphos, le thiométon, le triazophos, le triclorfon et le vamidothion ;
    (2) les antagonistes des canaux chlorure contrôlés par GABA, tels que par exemple
    les organochlores, p. ex. le chlordane et l'endosulfane (alpha-) ; ou
    les fiproles (phénylpyrazoles), p. ex. l'éthiprole, le fipronil, le pyrafluprole et le pyriprole ;
    (3) les modulateurs des canaux sodiques/bloquants des canaux sodiques dépendants de la tension, tels que par exemple
    les pyréthroïdes, p. ex. l'acrinathrine, l'alléthrine (d-cis-trans, d-trans), la bifenthrine, la bioalléthrine, la bioalléthrine-S-cyclopentényle, la bioresméthrine, la cycloprothrine, la cyfluthrine (bêta-), la cyhalothrine (gamma-, lambda-), la cyperméthrine (alpha-, bêta-, thêta-, zêta-), la cyphénothrine [isomères (1R)-trans], la deltaméthrine, la diméfluthrine, l'empenthrine [isomères (EZ)-(1R)], l'esfenvalérate, l'étofenprox, la fenpropathrine, le fenvalérate, le flucythrinate, la fluméthrine, le fluvalinate (tau-), l'halfenprox, l'imiprothrine, la métofluthrine, la perméthrine, la phénothrine [isomère (1R)-trans], la pralléthrine, la profluthrine, la pyréthrine (pyrèthre), la resméthrine, RU 15525, le silafluofen, la téfluthrine, la tétraméthrine [isomères (1R)], la tralométhrine, la transfluthrine et ZXI 8901 ; ou
    DDT ; ou le méthoxychlor ;
    (4) les agonistes des récepteurs d'acétylcholine nicotinergiques, tels que par exemple
    les néonicotinoïdes, p. ex. l'acétamiprid, la clothianidine, le dinotéfurane, l'imidacloprid, le nitenpyram, le thiacloprid, le thiaméthoxam ; ou
    la nicotine ;
    (5) les modulateurs des récepteurs d'acétylcholine allostériques (agonistes), tels que par exemple les spinosynes, p. ex. le spinétoram et le spinosad ;
    (6) les activateurs des canaux chlorure, tels que par exemple
    les avermectines/milbémycines, p. ex. l'abamectine, le benzoate d'émamectine, la lépimectine et la milbémectine ;
    (7) les analogues de l'hormone juvénile, p. ex. l'hydroprène, le kinoprène, le méthoprène ; ou le fénoxycarb ; le pyriproxyfen ;
    (8) les agents actifs à mécanisme d'action inconnu ou non spécifique, tels que par exemple
    les agents fumigants, p. ex. le bromure de méthyle et d'autres halogénures d'alkyle ; ou
    la chloropicrine ; le fluorure de sulfuryle ; le borax ; le tartrate d'antimoine et de potassium ;
    (9) les anorexigènes sélectifs, p. ex. la pymétrozine ; ou le flonicamide ;
    (10) les inhibiteurs de croissance des acariens, p. ex. la clofentézine, la diflovidazine, l'hexythiazox, l'étoxazole ;
    (11) les perturbateurs microbiens de la membrane intestinale des insectes, tels que p. ex. Bacillus thuringiensis sous-espèce israelensis, Bacillus sphaericus, Bacillus thuringiensis sous-espèce aizawai, Bacillus thuringiensis sous-espèce kurstaki, Bacillus thuringiensis sous-espèce tenebrionis, et les protéines végétales BT, p. ex. Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 ;
    (12) les inhibiteurs de la phosphorylation oxydative, les perturbateurs d'ATP, tels que par exemple le diafenthiuron ; ou
    les composés d'organoétain, p. ex. l'azocyclotine, la cyhexatine, l'oxyde de fenbutatine ; ou
    le propargite ; le tétradifon ;
    (13) les découpleurs de la phosphorylation oxydative par interruption des gradients de protons H, tels que par exemple le chlorfénapyr et DNOC ;
    (14) les antagonistes des récepteurs d'acétylcholine nicotinergiques, tels que par exemple le bensultap, le cartap (chlorhydrate de), le thiocylam et le thiosultap (-sodium) ;
    (15) les inhibiteurs de la biosynthèse de chitine, de type 0, tels que par exemple les benzoylurées, p. ex. le bistrifluron, le chlorfluazuron, le diflubenzuron, le flucycloxuron, le flufénoxuron, l'hexaflumuron, le lufénuron, le novaluron, le noviflumuron, le téflubenzuron et le triflumuron ;
    (16) les inhibiteurs de la biosynthèse de chitine, de type 1, tels que par exemple la buprofézine ;
    (17) les agents actifs perturbant la mue, tels que par exemple la cyromazine ;
    (18) les agonistes/perturbateurs d'ecdysone, tels que par exemple
    les diacylhydrazines, p. ex. le chromafénozide, l'halofénozide, le méthoxyfénozide et le tébufénozide ;
    (19) les agonistes octopaminergiques, tels que par exemple l'amitraz ;
    (20) les inhibiteurs du complexe III du transport d'électrons, tels que par exemple l'hydraméthylnon ; l'acéquinocyl ; le fluacrypyrim ;
    (21) les inhibiteurs du complexe I du transport d'électrons, par exemple du groupe des acaricides METI, p. ex. le fénazaquin, le fenpyroximate, le pyrimidifen, le pyridaben, le tébufenpyrad, le tolfenpyrad ; ou la roténone (Derris);
    (22) les bloquants des canaux sodiques dépendants de la tension, p. ex. l'indoxacarb ; la métaflumizone ;
    (23) les inhibiteurs d'acétyl-CoA-carboxylase, tels que par exemple les dérivés de l'acide tétronique, p. ex. le spirodiclofen et le spiromésifen ; ou les dérivés de l'acide tétramique, p. ex. le spirotétramate ;
    (24) les inhibiteurs du complexe IV du transport d'électrons, tels que p. ex. les phosphines, p. ex. le phosphure d'aluminium, le phosphure de calcium, la phosphine, le phosphure de zinc ; ou le cyanure ;
    (25) les inhibiteurs du complexe II du transport d'électrons, p. ex. le cyénopyrafen ;
    (28) les effecteurs du récepteur de ryanodine, tels que par exemple les diamides, p. ex. le flubendiamide, le chlorantraniliprole (rynaxypyr), le cyantraniliprole (cyazypyr), ainsi que le 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropyléthyl)carbamoyl]phényl}-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-carboxamide ou le carboxylate de méthyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-diméthylhydrazine ;
    d'autres agents actifs de mécanismes d'action inconnu, tels que par exemple l'azadirachtine, l'amidoflumet, le benzoximate, le bifénazate, le chinométhionate, le cryolite, le cyflumétofen, le dicofol, la fluensulfone (5-chloro-2-[(3,4,4-trifluorobut-3-én-1-yl)sulfonyl]-1,3-thiazole), le flufénérim, le pyridalyle et le pyrifluquinazon ; ainsi que les préparations à base de Bacillus firmus (1-1582, BioNeem, Votivo), ainsi que les composés actifs connus suivants :
    la 4-{[(6-bromopyrid-3-yl)méthyl](2-fluoroéthyl)amino}furan-2(5H)-one, la 4-{[(6-fluoropyrid-3-yl)méthyl](2,2-difluoroéthyl)amino}furan-2(5H)-one, la 4-{[(2-chloro-1,3-thiazol-5-yl)méthyl](2-fluoroéthyl)amino}furan-2(5H)-one, la 4-{[(6-chloropyrid-3-yl)méthyl](2-fluoroéthyl)amino}furan-2(5H)-one, la 4-{[(6-chloropyrid-3-yl)méthyl](2,2-difluoroéthyl)amino}furan-2(5H)-one, la 4-{[(6-chloro-5-fluoropyrid-3-yl)méthyl](méthyl)amino}furan-2(5H)-one, la 4-{[(5,6-dichloropyrid-3-yl)méthyl](2-fluoroéthyl)amino}furan-2(5H)-one, la 4-{[(6-chloro-5-fluoropyrid-3-yl)méthyl](cyclopropyl)amino}furan-2(5H)-one, la 4-{[(6-chloropyrid-3-yl)méthyl](cyclopropyl)amino}furan-2(5H)-one, la 4-{[(6-chloropyrid-3-yl)méthyl](méthyl)amino}furan-2(5H)-one, le [(6-chloropyridin-3-yl)méthyl](méthyl)oxido-λ4-sulfanylidène-cyanamide, le [1-(6-chloropyridin-3-yl)éthyl](méthyl)oxydo-λ4-sulfanylidène-cyanamide et ses diastéréomères (A) et (B)
    Figure imgb0116
    le [(6-trifluorométhylpyridin-3-yl)méthyl](méthyl)oxido-λ4-sulfanylidène-cyanamide, le sulfoxaflor, la 11-(4-chloro-2,6-diméthylphényl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tétradéc-11-én-10-one, la 3-(4'-fluoro-2,4-diméthylbiphényl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]déc-3-én-2-one, la 1-[2-fluoro-4-méthyl-5-[(2,2,2-trifluoroéthyl)sulfinyl]phényl]-3-(trifluorométhyl)-1H-1,2,4-triazol-5-amine,
    le carboxylate de [(3S,4aR,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,12b-diméthyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-décahydro-2H,11H-benzo[f]pyrano[4,3-b]chromén-4-yl]méthylcyclopropane,
    le 2-cyano-3-(difluorométhoxy)-N,N-diméthylbenzènesulfonamide,
    le 2-cyano-3-(difluorométhoxy)-N-méthylbenzènesulfonamide, le 2-cyano-3-(difluorométhoxy)-N-éthylbenzènesulfonamide, le 4-(difluorométhoxy)-N-éthyl-N-méthyl-1,2-benzothiazol-3-amine-1,1-dioxyde et
    la N-[1-(2,3-diméthylphényl)-2-(3,5-diméthylphényl)éthyl]-4,5-dihydro-1,3-thiazol-2-amine,
    et/ou au moins un agent actif fongicide supplémentaire choisi dans le groupe constitué par :
    (1) les inhibiteurs de la biosynthèse d'ergostérol, tels que par exemple l'aldimorph, l'azaconazole, le bitertanol, le bromuconazole, le cyproconazole, le diclobutrazole, le difénoconazole, le diniconazole, le diniconazol-M, le dodémorph, l'acétate de dodémorph, l'époxiconazole, l'étaconazole, le fénarimol, le fenbuconazole, le fenhexamide, la fenpropidine, le fenpropimorph, le fluquinconazole, le flurprimidol, le flusilazol, le flutriafol, le furconazole, le furconazole-cis, l'hexaconazole, l'imazalil, le sulfate d'imazalil, l'imibenconazole, l'ipconazole, le metconazole, le myclobutanil, la naftifine, le nuarimol, l'oxpoconazole, le paclobutrazole, le péfurazoate, le penconazole, la pipéraline, le prochloraz, le propiconazole, le prothioconazole, le pyributicarb, le pyrifénox, le quinconazole, le siméconazole, la spiroxamine, le tébuconazole, la terbinafine, le tétraconazole, le triadiméfon, le triadiménol, le tridémorph, le triflumizole, la triforine, le triticonazole, l'uniconazole, l'uniconazole-p, le viniconazole, le voriconazole, le 1-(4-chlorophényl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, le méthyl-1-(2,2-diméthyl-2,3-dihydro-1H-indén-1-yl)-1H-imidazole-5-carboxylate, le N'-{5-(difluorométhyl)-2-méthyl-4-[3-(triméthylsilyl)propoxy]phényl}-N-éthyl-N-méthylimidoformamide, le N-éthyl-N-méthyl-N'-{2-méthyl-5-(trifluorométhyl)-4-[3-(triméthylsilyl)propoxy]phényl}imidoformamide et l'O-[1-(4-méthoxyphénoxy)-3,3-diméthylbutan-2-yl]-1H-imidazole-1-carbothioate ;
    (2) les inhibiteurs de la respiration (inhibiteurs de la chaîne respiratoire), tels que par exemple le bixafen, le boscalid, la carboxine, le diflumétorim, le fenfuram, le fluopyram, le flutolanil, le fluxapyroxad, le furametpyr, le furmecyclox, l'isopyrazam, mélange du racémat syn-épimère 1RS,4SR,9RS et du racémat anti-épimère 1RS,4SR,9SR, l'isopyrazam (racémat anti-épimère), l'isopyrazam (énantiomère anti-épimère 1R,4S,9S), l'isopyrazam (énantiomère anti-épimère 1S,4R,9R), l'isopyrazam (racémat syn-épimère 1RS,4SR,9RS) l'isopyrazam (énantiomère syn-épimère 1R,4S,9R), l'isopyrazam (énantiomère syn-épimère 1S,4R,9S), le mépronil, l'oxycarboxine, le penflufen, le penthiopyrad, le sédaxane, le thifluzamide, le 1-méthyl-N-[2-(1,1,2,2-tétrafluoroéthoxy)phényl]-3-(trifluorométhyl)-1H-pyrazole-4-carboxamide, le 3-(difluorométhyl)-1-méthyl-N-[2-(1,1,2,2-tétrafluoroéthoxy)phényl]-1H-pyrazole-4-carboxamide, le 3-(difluorométhyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phényl]-1-méthyl-1H-pyrazole-4-carboxamide et le N-[1-(2,4-dichlorophényl)-1-méthoxypropan-2-yl]-3-(difluorométhyl)-1-méthyl-1H-pyrazole-4-carboxamide ;
    (3) les inhibiteurs de la respiration (inhibiteurs de la chaîne respiratoire) agissant sur le complexe III de la chaîne respiratoire, tels que par exemple l'amétoctradine, l'amisulbrom, l'azoxystrobine, le cyazofamide, la dimoxystrobine, l'énestroburine, la famoxadone, la fénamidone, la fluoxastrobine, le krésoxim-méthyl, la métominostrobine, l'orysastrobine, la picoxystrobine, la pyraclostrobine, la pyramétostrobine, la pyraoxystrobine, le pyribencarb, la trifloxystrobine, le (2E)-2-(2-{[6-(3-chloro-2-méthylphénoxy)-5-fluoropyrimidin-4-yl]oxy}phényl)-2-(méthoxyimino)-N-méthyléthanamide, le (2E)-2-(méthoxyimino)-N-méthyl-2-(2-{[({(1E)-1-[3-(trifluorométhyl)phényl]éthylidène}amino)oxy]méthyl}phé nyl)éthanamide, le (2E)-2-(méthoxyimino)-N-méthyl-2-{2-[(E)-({1-[3-(trifluorométhyl)phényl]éthoxy}imino)méthyl]phényl}étha namide, le (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phényléthényl]oxy}phényl)éthylidène]amino}oxy)méthyl]ph ényl}-2-(méthoxyimino)-N-méthyléthanamide, le (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophényl)but-3-én-2-ylidène]amino}oxy)méthyl]phényl}-2-(méthoxyimino)-N-méthyléthanamide, le 2-chloro-N-(1,1,3-triméthyl-2,3-dihydro-1H-indén-4-yl)pyridine-3-carboxamide, la 5-méthoxy-2-méthyl-4-(2-{[({(1E)-1-[3-(trifluorométhyl)phényl]éthylidène}amino)oxy]méthyl}phé nyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, le (2E)-2-{2-[({cyclopropyl[(4-méthoxyphényl)imino]méthyl}sulfanyl)méthyl]phényl}-3-méthoxyprop-2-énoate de méthyle, le N-(3-éthyl-3,5,5-triméthylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide, le 2-{2-[(2,5-diméthylphénoxy)méthyl]phényl}-2-méthoxy-N-méthylacétamide et le (2R)-2-{2-[(2,5-diméthylphénoxy)méthyl]phényl}-2-méthoxy-N-méthylacétamide ;
    (4) les inhibiteurs de la mitose et de la division cellulaire, tels que par exemple le bénomyl, le carbendazim, le chlorfénazole, le diéthofencarb, l'éthaboxam, le fluopicolid, le fubéridazole, le pencycuron, le thiabendazole, le thiophanate-méthyl, le thiophanate, le zoxamide, la 5-chloro-7-(4-méthylpipéridin-1-yl)-6-(2,4,6-trifluorophényl)[1,2,4]triazolo[1,5-a]pyrimidine et la 3-chloro-5-(6-chloropyridin-3-yl)-6-méthyl-4-(2,4,6-trifluorophényl)pyridazine ;
    (5) les composés à activité multi-site, tels que par exemple le mélange de Bordeaux, le captafol, le captane, le chlorothalonil, les préparations à base de cuivre telles que l'hydroxyde de cuivre, le naphténate de cuivre, l'oxyde de cuivre, l'oxychlorure de cuivre, le sulfate de cuivre, le dichlofluanide, le dithianon, la dodine, la base libre de dodine, le ferbam, le fluorofolpet, le folpet, la guazatine, l'acétate de guazatine, l'iminoctadine, l'albésilate d'iminoctadine, le triacétate d'iminoctadine, le mankupfer, le mancozeb, le maneb, le métiram, le métiram de zinc, l'oxine-cuivre, la propamidine, le propineb, le soufre et les préparations à base de soufre telles que par exemple le polysulfure de calcium, le thiram, le tolylfluanide, le zineb et le ziram ;
    (6) les inducteurs de résistance, tels que par exemple l'acibenzolar-S-méthyl, l'isotianil, le probénazole et le tiadinil ;
    (7) les inhibiteurs de la biosynthèse d'acides aminés et de protéines, tels que par exemple l'andoprim, la blasticidine-S, le cyprodinil, la kasugamycine, le chlorhydrate de kasugamycine hydraté, le mépanipyrim et le pyriméthanil ;
    (8) les inhibiteurs de la production d'ATP, tels que par exemple l'acétate de fentine, le chlorure de fentine, l'hydroxyde de fentine et le silthiofam ;
    (9) les inhibiteurs de synthèse de la paroi cellulaire, tels que par exemple le benthiavalicarb, le diméthomorph, le flumorph, l'iprovalicarb, le mandipropamide, les polyoxines, le polyoxorim, la validamycine A et le valifénalate ;
    (10) les inhibiteurs de la synthèse de lipides et de membranes, tels que par exemple le biphényle, le chloroneb, le dicloran, l'édifenphos, l'étridiazole, l'iodocarb, l'iprobenfos, l'isoprothiolan, le propamocarb, le chlorhydrate de propamocarb, le prothiocarb, le pyrazophos, le quintozène, le tecnazène et le tolclofos-méthyl ;
    (11) les inhibiteurs de la biosynthèse de mélanine, tels que par exemple le carpropamide, le diclocymet, le fénoxanil, le phthalide, la pyroquilone et le tricyclazole ;
    (12) les inhibiteurs de la synthèse d'acides nucléiques, tels que par exemple le bénalaxyl, le bénalaxyl-M (kiralaxyl), le bupirimate, le clozylacon, le diméthirimol, l'éthirimol, le furalaxyl, l'hymexazole, le métalaxyl, le métalaxyl-M (méfénoxam), l'ofurace, l'oxadixyl, l'acide oxolique ;
    (13) les inhibiteurs de la transduction de signaux, tels que par exemple le chlozolinate, le fenpiclonil, le fludioxonil, l'iprodione, la procymidone, le quinoxyfen et la vinclozoline ;
    (14) les découpleurs, tels que par exemple le binapacryl, le dinocap, la férimzone, le fluazinam et le meptyldinocap ;
    (15) d'autres composés, tels que par exemple le benthiazole, la béthoxazine, la capsimycine, la carvone, le chinométhionate, la chlazafénone, le cufraneb, le cyflufénamide, le cymoxanil, le cyprosulfamide, le dazomet, le débacarb, le dichlorophène, la diclomézine, le difenzoquat, le méthylsulfate de difenzoquat, la diphénylamine, l'écomat, la fenpyrazamine, le flumétover, le fluoromid, le flusulfamide, le flutianil, le fosétyl-aluminium, le fosétyl-calcium, le fosétyl-sodium, l'hexachlorobenzène, l'irumamycine, le méthasulfocarb, l'isothiocyanate de méthyle, la métrafénone, la mildiomycine, la natamycine, le diméthyldithiocarbamate de nickel, le nitrothal-isopropyl, l'octhilinone, l'oxamocarb, l'oxyfenthiine, le pentachlorophénol et ses sels, la phénothrine, l'acide phosphorique et ses sels, le fosétylate de propamocarb, la propanosine-sodium, le proquinazide, la pyrrolnitrine, la tébufloquine, le técloftalam, le tolnifanid, le triazoxyde, le trichlamide, le zarilamide, la 1-(4-{4-[(5R)-5-(2,6-difluorophényl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}pipéridin-1-yl)-2-[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]éthanone, la 1-(4-{4-[(5S)-5-(2,6-difluorophényl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}pipéridin-1-yl)-2-[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]éthanone, la 1-(4-{4-[5-(2,6-difluorophényl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}pipéridin-1-yl)-2-[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]éthanone, le 1-(4-méthoxyphénoxy)-3,3-diméthylbutan-2-yl-1H-imidazol-1-carboxylate, la 2,3,5,6-tétrachloro-4-(méthylsulfonyl)pyridine, la 2,3-dibutyl-6-chlorothiéno[2,3-d]pyrimidin-4(3H)-one, la 2-[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phényl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}pipéridin-1-yl)éthanone, la 2-[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phényl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}pipéridin-1-yl)éthanone, la 2-[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phényl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]pipéridin-1-yl}éthanone, la 2-butoxy-6-iodo-3-propyl-4H-chromén-4-one, la 2-chloro-5-[2-chloro-1-(2,6-difluoro-4-méthoxyphényl)-4-méthyl-1H-imidazol-5-yl]pyridine, le 2-phénylphénol et ses sels, le 3,4,5-trichloropyridine-2,6-dicarbonitrile, la 3-[5-(4-chlorophényl)-2,3-diméthyl-1,2-oxazolidin-3-yl]pyridine, la 3-chloro-5-(4-chlorophényl)-4-(2,6-difluorophényl)-6-méthylpyridazine, la 4-(4-chlorophényl)-5-(2,6-difluorophényl)-3,6-diméthylpyridazine, le 5-amino-1,3,4-thiadiazole-2-thiol, le 5-chloro-N'-phényl-N'-(prop-2-yn-1-yl)thiophène-2-sulfonohydrazide, la 5-méthyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, le (2Z)-3-amino-2-cyano-3-phénylprop-2-énoate d'éthyle, le N-(4-chlorobenzyl)-3-[3-méthoxy-4-(prop-2-yn-1-yloxy)phényl]propanamide, le N-[(4-chlorophényl)(cyano)méthyl]-3-[3-méthoxy-4-(prop-2-yn-1-yloxy)phényl]propanamide, le N-[(5-bromo-3-chloropyridin-2-yl)méthyl]-2,4-dichloropyridine-3-carboxamide, le N-[1-(5-bromo-3-chloropyridin-2-yl)éthyl]-2,4-dichloropyridine-3-carboxamide, le N-[1-(5-bromo-3-chloropyridin-2-yl)éthyl]-2-fluoro-4-iodopyridine-3-carboxamide, le N-{(E)-[(cyclopropylméthoxy)imino][6-(difluorométhoxy)-2,3-difluorophényl]méthyl}-2-phénylacétamide, le N-{(Z)-[(cyclopropylméthoxy)imino][6-(difluorométhoxy)-2,3-difluorophényl]méthyl}-2-phénylacétamide, le N-méthyl-2-(1-{[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]acétyl}pipéridin-4-yl)-N-(1,2,3,4-tétrahydronaphtalén-1-yl)-1,3-thiazol-4-carboxamide, le N-méthyl-2-(1-{[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]acétyl}pipéridin-4-yl)-N-[(1R)-1,2,3,4-tétrahydronaphtalén-1-yl]-1,3-thiazole-4-carboxamide, le N-méthyl-2-(1-{[5-méthyl-3-(trifluorométhyl)-1H-pyrazol-1-yl]acétyl}pipéridin-4-yl)-N-[(1S)-1,2,3,4-tétrahydronaphtalén-1-yl]-1,3-thiazol-4-carboxamide, le pentyl-{6-[({[(1-méthyl-1H-tétrazol-5-yl)(phényl)méthylidène]amino}oxy)méthyl]pyridin-2-yl}carbamate, l'acide phénazine-1-carboxylique, le quinolin-8-ol et le sulfate de quinolin-8-ol (2:1) ;
    (16) d'autres composés, tels que par exemple le 1-méthyl-3-(trifluorométhyl)-N-[2'-(trifluorométhyl)biphényl-2-yl]-1H-pyrazol-4-carboxamide, le N-(4'-chlorobiphényl-2-yl)-3-(difluorométhyl)-1-méthyl-1H-pyrazole-4-carboxamide, le N-(2',4'-dichlorobiphényl-2-yl)-3-(difluorométhyl)-1-méthyl-1H-pyrazole-4-carboxamide, le 3-(difluorométhyl)-1-méthyl-N-[4'-(trifluorométhyl)biphényl-2-yl]-1H-pyrazole-4-carboxamide, le N-(2',5'-difluorobiphényl-2-yl)-1-méthyl-3-(trifluorométhyl)-1H-pyrazole-4-carboxamide, le 3-(difluorométhyl)-1-méthyl-N-[4'-(prop-1-yn-1-yl)biphényl-2-yl]-1H-pyrazole-4-carboxamide, le 5-fluoro-1,3-diméthyl-N-[4'-(prop-1-yn-1-yl)biphényl-2-yl]-1H-pyrazole-4-carboxamide, le 2-chloro-N-[4'-(prop-1-yn-1-yl)biphényl-2-yl]pyridine-3-carboxamide, le 3-(difluorométhyl)-N-[4'-(3,3-diméthylbut-1-yn-1-yl)biphényl-2-yl]-1-méthyl-1H-pyrazole-4-carboxamide, le N-[4'-(3,3-diméthylbut-1-yn-1-yl)biphényl-2-yl]-5-fluoro-1,3-diméthyl-1H-pyrazole-4-carboxamide, le 3-(difluorométhyl)-N-(4'-éthynylbiphényl-2-yl)-1-méthyl-1H-pyrazole-4-carboxamide, le N-(4'-éthynylbiphényl-2-yl)-5-fluoro-1,3-diméthyl-1H-pyrazole-4-carboxamide, le 2-chloro-N-(4'-éthynylbiphényl-2-yl)pyridine-3-carboxamide, le 2-chloro-N-[4'-(3,3-diméthylbut-1-yn-1-yl)biphényl-2-yl]pyridine-3-carboxamide, le 4-(difluorométhyl)-2-méthyl-N-[4'-(trifluorométhyl)biphényl-2-yl]-1,3-thiazole-5-carboxamide, le 5-fluoro-N-[4'-(3-hydroxy-3-méthylbut-1-yn-1-yl)biphényl-2-yl]-1,3-diméthyl-1H-pyrazole-4-carboxamide, le 2-chloro-N-[4'-(3-hydroxy-3-méthylbut-1-yn-1-yl)biphényl-2-yl]pyridine-3-carboxamide, le 3-(difluorométhyl)-N-[4'-(3-méthoxy-3-méthylbut-1-yn-1-yl)biphényl-2-yl]-1-méthyl-1H-pyrazole-4-carboxamide, le 5-fluoro-N-[4'-(3-méthoxy-3-méthylbut-1-yn-1-yl)biphényl-2-yl]-1,3-diméthyl-1H-pyrazole-4-carboxamide, le 2-chloro-N-[4'-(3-méthoxy-3-méthylbut-1-yn-1-yl)biphényl-2-yl]pyridine-3-carboxamide, la (5-bromo-2-méthoxy-4-méthylpyridin-3-yl)(2,3,4-triméthoxy-6-méthylphényl)méthanone et le N-[2-(4-{[3-(4-chlorophényl)prop-2-yn-1-yl]oxy}-3-méthoxyphényl)éthyl]-N2-(méthylsulfonyl)valinamide.
  7. Composition contenant au moins un composé de formule (I) selon l'une quelconque des revendications 1 à 2 ou une composition d'agents actifs selon la revendication 6, ainsi qu'au moins un promoteur de pénétration.
  8. Composés de formule générale (II-A) selon la revendication 3
    Figure imgb0117
     dans laquelle A1, B0, B2 ont les significations selon l'une quelconque des revendications 1 à 2, et B1 et B3 représentent l'hydrogène.
  9. Composé de formule générale (III-A) selon la revendication 3
    Figure imgb0118
     dans laquelle A1, B0 et B2 ont les significations selon l'une quelconque des revendications 1 à 2, et B1 et B3 représentent l'hydrogène.
  10. Composés de formule générale (IV-A) selon la revendication 3
    Figure imgb0119
     dans laquelle
    B1 et B3 représentent l'hydrogène, et
    B0 représente hydrogène, méthyle, éthyle, fluor, chlore, méthoxy, cyano, CHF2, CF3 ou OCF3,
    B2 représente hydrogène, méthyle, éthyle, fluor, chlore, méthoxy, cyano, CHF2, CF3 ou OCF3.
  11. Composé de formule générale (V) selon la revendication 3
    Figure imgb0120
     dans laquelle
    B1 et B3 représentent l'hydrogène,
    A1 représente CHF2,
    B0 représente méthyle, éthyle, fluor, chlore, méthoxy, cyano, CHF2, CF3 ou OCF3,
    B2 représente hydrogène, éthyle, fluor, chlore, cyano, CHF2, CF3 ou OCF3.
  12. Compositions agrochimiques, caractérisées en ce qu'elles contiennent au moins un composé de formule (I) selon les revendications 1 à 2 ou une composition selon l'une quelconque des revendications 6 à 7, ainsi que des extendeurs et/ou des substances tensioactives.
  13. Utilisation de composés de formule (I) selon l'une quelconque des revendications 1 à 2 ou d'une composition selon l'une quelconque des revendications 6, 7 ou 12, pour lutter contre les animaux nuisibles dans le cadre de la protection des plantes ou de la protection des matériaux.
  14. Composé de formule (I) selon l'une quelconque des revendications 1 à 2 ou composition selon l'une quelconque des revendications 6, 7 ou 12, destiné à une utilisation dans un procédé dans le secteur de la médecine vétérinaire.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103190422A (zh) * 2013-05-04 2013-07-10 青岛奥迪斯生物科技有限公司 一种含有甲氧虫酰肼与灭多威的杀虫组合物

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005022147A1 (de) * 2005-04-28 2006-11-02 Bayer Cropscience Ag Wirkstoffkombinationen
EP2274982A1 (fr) * 2009-07-16 2011-01-19 Bayer CropScience AG Utilisation de phényltriazole pour combattre les insectes et les tétranyques par arrosage, application au goutte-à-goutte ou par immersion ou par le traitement de semences
EP2454242B1 (fr) * 2009-07-16 2014-10-15 Bayer CropScience AG Procédé de préparation de dérivés 3-triazolyl-sulfoxyde chiraux
CN104430378A (zh) * 2009-07-16 2015-03-25 拜尔农作物科学股份公司 含苯基三唑的协同活性物质结合物
KR20120060217A (ko) * 2009-08-20 2012-06-11 바이엘 크롭사이언스 아게 살비제 및 살충제로 사용하기 위한 3-트리아졸릴페닐-치환된 설파이드 유도체
CN102246807B (zh) * 2011-07-21 2013-06-12 青岛奥迪斯生物科技有限公司 一种含有四氟醚唑与硅氟唑的杀菌组合物
EP2604118A1 (fr) * 2011-12-15 2013-06-19 Bayer CropScience AG Combinaisons d'ingrédients actifs dotées de propriétés insecticides et acaricides
CN102816133B (zh) * 2012-08-01 2014-07-02 南开大学 一类5-氯-1,2,3-噻二唑-4-丙烯酸衍生物及其制备方法和用途
CN102816134B (zh) * 2012-08-03 2014-07-02 南开大学 一类含1,2,3-噻二唑的硫(砜)亚胺类化合物及其制备方法和用途
CN102993109A (zh) * 2012-12-03 2013-03-27 浙江工业大学 一种脒化合物的制备方法
CN103355279B (zh) * 2013-07-19 2014-11-26 江苏省农业科学院 用于防治设施作物蚜虫的电热灭蚜方法及其所用灭蚜液
CN104026136B (zh) * 2014-06-16 2015-07-15 深圳诺普信农化股份有限公司 一种农用杀菌组合物
CA2979549C (fr) 2015-03-27 2023-09-26 Bayer Cropscience Lp Procedes et compositions permettant de reduire l'infestation fongique et d'ameliorer la qualite de l'herbe
CN106699764A (zh) * 2016-12-19 2017-05-24 浙江先锋科技股份有限公司 一种双氯磺草胺的制备方法
CN110455962A (zh) * 2019-09-11 2019-11-15 中国检验检疫科学研究院 一种植物食品中消螨多残留量的测定方法
JP7166487B2 (ja) 2020-03-31 2022-11-07 日立建機株式会社 深礎掘削機

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005097784A1 (fr) * 2004-04-07 2005-10-20 Bayer Healthcare Ag Derives d'acide phenylthioacetique et leur utilisation
WO2011006646A1 (fr) * 2009-07-16 2011-01-20 Bayer Cropscience Ag Procédé de préparation de dérivés 3-triazolyl-sulfoxyde chiraux

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7528974A (en) * 1973-11-13 1976-06-10 Commonwealth Scientific And Industrial Research Organization Triazoles
EP0285893B1 (fr) * 1987-03-27 1992-03-18 Kumiai Chemical Industry Co., Ltd. Dérivé de phényltriazole et insecticide
JPH01230562A (ja) * 1987-03-27 1989-09-14 Kumiai Chem Ind Co Ltd フェニルトリアゾール誘導体及び殺虫剤
EP0539588A1 (fr) 1990-07-05 1993-05-05 Nippon Soda Co., Ltd. Derive d'amine
JP3720131B2 (ja) * 1995-08-15 2005-11-24 富士写真フイルム株式会社 熱現像感光材料
AU3536699A (en) * 1998-04-27 1999-11-16 Ihara Chemical Industry Co. Ltd. 3-arylphenyl sulfide derivatives and insecticides and miticides
JP4407062B2 (ja) * 2001-02-14 2010-02-03 宇部興産株式会社 ジフェニルジスルフィド誘導体の製造法
UA79404C2 (en) 2003-10-02 2007-06-11 Basf Ag 2-cyanobenzenesulfonamide for controlling pests
RS54576B1 (en) * 2004-02-18 2016-06-30 Ishihara Sangyo Kaisha, Ltd. ANTRANYLAMIDES, THE PROCEDURE FOR THEIR MANUFACTURE AND THE MEANS OF CONTROL OF THE DAMAGES CONTAINING THEM
NZ553200A (en) 2004-10-20 2009-09-25 Kumiai Chemical Industry Co 3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient
ATE469124T1 (de) 2004-11-26 2010-06-15 Basf Se Neue 2-cyano-3- (halogen)alkoxybenzolsulfonamidverbindungen zur bekämpfung tierischer schädlinge
DE102005008021A1 (de) * 2005-02-22 2006-08-24 Bayer Cropscience Ag Spiroketal-substituierte cyclische Ketoenole
AU2006226300A1 (en) 2005-03-24 2006-09-28 Basf Aktiengesellschaft 2-cyanobenzenesulfonamide compounds for seed treatment
TWI388282B (zh) 2005-06-01 2013-03-11 Meiji Seika Pharma Co Ltd 害蟲控制劑
US7491738B2 (en) * 2005-06-01 2009-02-17 Meiji Seika Kaisha, Ltd. Pest control agents
PT1937664E (pt) 2005-10-14 2011-07-07 Sumitomo Chemical Co Composto de hidrazida e utilização pesticida do mesmo
WO2007057407A2 (fr) 2005-11-21 2007-05-24 Basf Se Procedes insecticides utilisant des derives de 3-amino-1,2-benzisothiazole
TWI398433B (zh) 2006-02-10 2013-06-11 Dow Agrosciences Llc 殺蟲性之ｎ-取代（６-鹵烷基吡啶-３-基）烷基磺醯亞胺
DE102006015468A1 (de) * 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
DE102006015467A1 (de) * 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
DE102006015470A1 (de) * 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
JP2007284356A (ja) 2006-04-12 2007-11-01 Kumiai Chem Ind Co Ltd ３−トリアゾリルフェニルスルフィド誘導体及びそれを有効成分として含有する農園芸用殺虫・殺ダニ・殺線虫剤
TWI381811B (zh) 2006-06-23 2013-01-11 Dow Agrosciences Llc 用以防治可抵抗一般殺蟲劑之昆蟲的方法
DE102006057036A1 (de) 2006-12-04 2008-06-05 Bayer Cropscience Ag Biphenylsubstituierte spirocyclische Ketoenole
CN101621928A (zh) 2007-03-01 2010-01-06 巴斯夫欧洲公司 包含氨基噻唑啉化合物的杀虫活性混合物
CN101910140A (zh) * 2007-11-30 2010-12-08 庵原化学工业株式会社 (1h-1,2,4-三唑-1-基)芳基化合物及其制备方法
JP5167283B2 (ja) * 2008-01-10 2013-03-21 北興化学工業株式会社 フェニルトリアゾリノン類の製造法
KR101638991B1 (ko) * 2008-05-07 2016-07-12 바이엘 인텔렉쳐 프로퍼티 게엠베하 상승적 활성 성분 배합물
EP2269455A1 (fr) * 2009-06-24 2011-01-05 Bayer CropScience AG Combinaisons de biopesticides et d'insecticides
EP2274982A1 (fr) * 2009-07-16 2011-01-19 Bayer CropScience AG Utilisation de phényltriazole pour combattre les insectes et les tétranyques par arrosage, application au goutte-à-goutte ou par immersion ou par le traitement de semences
CN104430378A (zh) * 2009-07-16 2015-03-25 拜尔农作物科学股份公司 含苯基三唑的协同活性物质结合物
KR20120060217A (ko) * 2009-08-20 2012-06-11 바이엘 크롭사이언스 아게 살비제 및 살충제로 사용하기 위한 3-트리아졸릴페닐-치환된 설파이드 유도체

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005097784A1 (fr) * 2004-04-07 2005-10-20 Bayer Healthcare Ag Derives d'acide phenylthioacetique et leur utilisation
WO2011006646A1 (fr) * 2009-07-16 2011-01-20 Bayer Cropscience Ag Procédé de préparation de dérivés 3-triazolyl-sulfoxyde chiraux

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE PUBCHEM [online] NCBI; 5 December 2007 (2007-12-05), Database accession no. CID 20661897 *
MODERHACK DIETRICH ET AL: "Comparison of N-isomers of 1,2,4-triazolecarboxaldehydes", CHEMIKER ZEITUNG, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 115, no. 10, 1 January 1991 (1991-01-01), pages 271 - 275, XP009138488, ISSN: 0009-2894 *

Cited By (2)

* Cited by examiner, † Cited by third party
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CN103190422A (zh) * 2013-05-04 2013-07-10 青岛奥迪斯生物科技有限公司 一种含有甲氧虫酰肼与灭多威的杀虫组合物
CN103190422B (zh) * 2013-05-04 2017-12-05 青岛奥迪斯生物科技有限公司 一种含有甲氧虫酰肼与灭多威的杀虫组合物

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CN102573479B (zh) 2015-04-22
JP2013502386A (ja) 2013-01-24
JP5736373B2 (ja) 2015-06-17
KR20120089458A (ko) 2012-08-10
BR112012003698A2 (pt) 2015-09-08
BR112012003698B1 (pt) 2018-12-26
IN2012DN01298A (fr) 2015-06-05
MX2012001969A (es) 2012-03-29
WO2011029506A1 (fr) 2011-03-17
EP2467021A1 (fr) 2012-06-27
ES2559012T3 (es) 2016-02-10
US20110045104A1 (en) 2011-02-24
US8632767B2 (en) 2014-01-21

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